Monobasic potassium phosphate → methyl N-(4-bromo-5-methylisoxazol-3-yl)leucinate

HRID 1744106노트

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HRID 1744106 반응식
[Br:1][C:2]1[C:3]([N:8](C(OCC(Cl)(Cl)Cl)=O)[C@H:9]([C:14]([O:16][CH3:17])=[O:15])[CH2:10][CH:11]([CH3:13])[CH3:12])=[N:4][O:5][C:6]=1[CH3:7].OP([O-])(O)=O.[K+]>[Zn].C1COCC1>[Br:1][C:2]1[C:3]([NH:8][C@H:9]([C:14]([O:16][CH3:17])=[O:15])[CH2:10][CH:11]([CH3:13])[CH3:12])=[N:4][O:5][C:6]=1[CH3:7]

참가 물질

5

반응물 2

HCID 516951Monobasic potassium phosphateHCID 69152129methyl N-(4-bromo-5-methylisoxazol-3-yl)-N-[(2,2,2-trichloroethoxy)carbonyl]leucinate

생성물 1

HCID 69152086methyl N-(4-bromo-5-methylisoxazol-3-yl)leucinate

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 8028Tetrahydrofuran용매

실험 절차

To a dry THF solution (20 mL) of methyl N-(4-bromo-5-methylisoxazol-3-yl)-N-[(2,2,2-trichloroethoxy)carbonyl]leucinate (1.19 g, 2.47 mmol) and activated zinc (10.1 g, 154 mmol) was added ca. 10 mL of 1 M KH2PO4 (10 mmol) at 0° C. The mixture was stirred for 1.5 hours, filtered through celite, washed with 150 mL ethyl acetate, and concentrated to a small volume. The mixture was then partitioned between ethyl acetate and saturated aqueous sodium bicarbonate, washed with brine, dried over sodium sulphate and concentrated in vacuo. The crude product was purified by flash chromatography (20% ethyl acetate/hexane) to afford methyl N-(4-bromo-5-methylisoxazol-3-yl)leucinate.

후처리

  1. filtrationfiltered through celite
  2. washwashed with 150 mL ethyl acetate
  3. concentrationconcentrated to a small volume
  4. customThe mixture was then partitioned between ethyl acetate and saturated aqueous sodium bicarbonate
  5. washwashed with brine
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by flash chromatography (20% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-0b8e3aed12184076909fe9851eebd254
출처 데이터셋
uspto-grants-2006_03
특허 번호
US07012075B2

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